Space Cobra

Space Adventure Cobra is Cowboy Bebop's best known source of inspiration. The citationism is exasperated, especially to American culture, but it is not yet influenced by postmodernism of the 90s. Both works are born to entertain the spectator. Science fiction with evasive purpose. 

This is the closest to the feel of Cowboy bebop I have found out there. Space Cobra is a true Masterpiece extremely under appreciated. If you're a fan of Cowboy bebop's futuristic, synthwavy, spacial feel, then you'll absolutely love Cobra. 

Both series set in space and deal with crime and adventures. Similar style of main characters. Both main characters - an epic womanizers. Both has the robots as partners. And maybe the robot in Space Dandy will turn into Android Lady too, who knows )  

Space Cobra practically inspired the whole genre of badass space dudes so ofc you should watch both because they go hand in hand. 

The similarities between two anime are too many to count but here are some: -Both anime have a semi-episodic structure with an emphasis on adventure in space -Both anime have an anti-hero as the MC and a female android as a companion/partner -In both anime evil pirates are the main enemy in addition to some other enemies -In both anime there is some sort of special police force; Galactic Patrol in Cobra, Angel Links in Outlaw Star -In both anime the main character has a special weapon Psychogun in Cobra and Caster gun in Outlaw Star -Both anime fall under the space opera genre and as expected from the genre the characters visit different planets throughout the series -In both anime characters use a specially built spaceship with some cool features -Both anime has a plot about searching for a secret treasure all the while competing against evil pirates to reach it first -In both anime the leader of the evil pirates is a mysterious character who wears some kind of mask -Both anime have an episode where the main character poses as a wrestler Last but not least, even though many people compare Outlaw Star to Cowboy Bebop (since it's much better known unlike Cobra) in fact the similarities between two anime are pretty much superficial like both having the space theme and anti-hero vibe going on, whereas similarities between Cobra and Outlaw Star make them perfect companion pieces .  read more 

It is no exagerration to say that Space Cobra is Lupin III, but in space. 

Both "Dirty Pair" and "Space Cobra" tell action packed stories of space adventuring and bounty hunting pairs of badasses. Both are full of nuts-to-butts action as their first priority. Both shows have very similar aesthetics and boast some of the best visuals in anime to this day. Biggest difference between the two is that Dirty Pair is a pair of sexy ladies while Cobra is an incredibly manly man with a robot companion. Cobra is a lot more focused and has some longer arcs, while Dirty Pair is all over the place and fully episodic. Both series follow their first seasons with a bunch of OVAs and a movie, while Cobra's sequels are worse than the First season, Dirty Pair's sequels kick ass over the first season.  read more 

While the setting and plot are different between the two series... Both series are quite similar in tone. The characters feel like they're written very similarly. Both Lupin and Cobra share many personality traits, and the antagonists in both series feel like they're written similarly as well. The art is pretty similar, too, with both series featuring detailed hand-painted CELs, and lots of expressive motion lines during fast-paced chase scenes. Even the soundtrack for both series are reminiscent of each other, featuring a lot of the same 70s disco undertones, and similar sounding stings and audio cues. If you like one, I would find it hard to believe that you wouldn't like the other. read more 

Both series features a MANLY protagonist who are placed in various scenarios from assassination, adventure & espionage. Cobra is set in a Star Wars-like world while Golgo 13 is placed in a realistic urban setting. Cobra features aliens, robots & nude women while Golgo 13 features assassins, mobsters, & passionate sex scenes. These animes are made by men for men as they're full of action, guns, fights, women & overall MANLY!  

Ablonde outlaw dressed all in red with a gun hidden in his arm and an easy smile. He is a Legend, pursued by other outlaws looking to make names for themselves by outgunning a desperado of his caliber, but every person that he encounters underestimates him because he seems "too goofy" to be THE LEGEND. Space Adventure Cobra's DNA is all over the space western genre, but nowhere more obviously than in Trigun.